I understand why you and your H are worried. Jobs can be hard to come by and skiing seems frivolous. I am a skier myself and used to go on lots of trips, but was never willing to sleep in a car. Now that it is clear when your financial support ends, I think it will all sink in. I wonder if he sees this as his last big trip before he settles into adult life. Regardless, it may be. I hope he figures it out sooner rather than later. Time now for his parents to step back and try not to watch too closely as these are his choices to live with now.
I would not be disappointed that he wants to ski over his last Spring Break. Reading between the lines, it sounds like you/your husband are disappointed that he is not being more aggressive/more focused on finding his first job, but my perspective is that as someone who began working immediately after college, I wish I had taken some time for myself before starting real work. It’s tough to go back, once you get a professional job. I wish I had given myself more time, but I was very eager to start my career. Regarding skiing-my husband is an avid skiier. When we first met, it was an issue because he went to VT every weekend in the Winter, and our budding relationship was put on hold. Then I was folded into the skiing. Now we’re married with a child and we’ve been renting our own ski house for the last few years, and he also takes a trip out West each year… Our child is an excellent skiier already. Besides all of this skiing he is an exec at an Fortune 100 company in NYC, so he is no slacker. Skiing is an excellent way for intense people to burn off stress, in my experience. Sleeping in the car is not unusual, actually - I don’t do it, and husband is too old for it now, but he has, and it sounds like generally there are other young people doing the same thing at the ski areas. I know the mountain that we go to has no problem with it. Just reading your post-you are worried about what the PT employer thinks, you are worried about the girlfriend, you are worried about his driving on snowy roads…parents worry, of course, but what if you ry to train your thoughts on to more positive things? You say he is honest, it sounds like his PT job goes a long way in Pittsburgh, sounds like the GF is nice, his relationship with his sister is close, he is graduating with a difficult degree that has some employment options…sounds like there is a lot to be happy about.
Gosh! Some of you stress about fairly minor things. Young people - especially males - sleeping in cars is no big deal. No guns needed. Haha. Many of my kids’ friends have old SUVs and trucks specifically rigged for sleeping in the back and there are free/cheap mountain huts for backcountry skiing, plus people do winter camping as well. Mine rarely has to pay for lodging.
I need to tell my kids what an easygoing parent I am. I don’t think I’m getting sufficient credit. 
I’m almost 50 years old. I slept in a car 2 years to go snowboarding in the morning. It’s not about the $, it’s about he adventure! Let the kid have some fun before he chooses to settle down.
@toomanyteens, so glad to hear that you and your H are supporting S’s graduation. And it’s perfectly acceptable to give him a July 1 cutoff. It sounds like you are doing all you can to be supportive.
I’m going to stick up for the op. It’s fine for someone to have a hobby, even an obsession. My bil is a very successful person who is very driven in whatever he does. That includes whatever sports he does.
But according to the OP, the obsession is not what they are worried about expressly. But the reckless behavior that seems to accompany his sport. It sounds like he is taking risks and that is what the parent is most worried about. I have kids and sometimes they do things I worry about, my D likes to weightlift. I love that she’s into fitness and love that she posts videos of herself with new PR’s. But if she was posting videos or telling me that she is trying new weights without the proper safety precautions, I would be so upset. I’m on pins and needles just looking at her lifting, but I know she’s doing it safely and that she always has spotters.
It sounds like this kid skis without a helmet at times and has other behavior which the OP and her H are concerned about. I would be very upset about that myself. It’s not just that he wants to ski all the time.
@deb922 Exactly the risks! What if gets hurt? And these days people do get arrested for sleeping in their cars-- it isn’t like it used to be where you could sort of do that kind of thing. He has been known to trespass and try to ski without a pass etc. – all which could be bad news for a background check for employment if he gets himself arrested.
– and it is all well and good to say let him have some time blah blah, but on whose dime exactly? Where will he live, how will he pay his expenses? We have 5 kids and we do what we can for them after two very difficult and costly divorces and no financial support from the other parents, so the luxury of not settling down to a job isn’t there. The practical reality is that we cannot afford to have adult kids who are done with school not actively supporting themselves.
“and it is all well and good to say let him have some time blah blah, but on whose dime exactly? Where will he live, how will he pay his expenses?”
On his dime. You’ve made that clear to him, correct, effective 7/1? Then, it is his choice. He doesn’t sound like a stupid kid.
There are PLENTY of places where one can sleep in their car without being arrested. Plenty. It’s one thing to worry but don’t go tilting at windmills. 
I really get the feeling there is more here beyond the skiing/job thing in terms of angst and family dynamics. It just feels out of proportion to me.
I was in the same boat @toomanyteens! The same reality that once the kids were done with school, they needed to support themselves. They needed to pay their own cell phones and get their own health insurance.
I am aware that for many families (many here and many IRL) that isn’t the case. Everyone has their comfort zones, but for my family paying for college was a gift we gave them. After that, they were made aware that they needed to be independent.
Admittedly I haven’t read the entire thread so I don’t know if someone pointed this out already…but it’s only February. Late February, yes, but still just February. Assuming that OP’s son is graduating in May, he’s still got three months to secure a full-time job. There are lots of students in lots of fields who don’t have a job secured until the latter half of second semester - not all employers recruit super early in the school year.
I would expect a senior to spend his last spring break doing something fun he wanted to do.
Also, the girlfriend, I assume, is an independent person. If she just moved there two weeks ago, she should be getting out into the city meeting people and trying to put down some roots herself. The boyfriend being gone for 10 days shouldn’t be a huge issue.
It seems to be a luxury you’ve been providing for your 22-year-old daughter for several years. Last month you posted that she partied through her first year of college and got tossed off her equestrian team, so you brought her home and let her enroll in a cc while living with your ex. She changed majors a couple times, repeated classes, and came away with very few credits. She lived with a boyfriend, and when that fell apart you helped her move in with a friend of yours. After she lost her job she moved back in with your ex. Now she wants to move in with a friend, and you and your husband are ready to draw the line and refuse to continue paying her tuition if she moves. However, it appears that if she decides to stay with your ex, you’ll continue to pay.
Your stepson, on the other hand, seems to have completed his degree in 4 years, has plans to get a job after graduation, and pays for his own ECs. My youngest has 3 learning disorders so I understand that kids are different and have different needs, but you live in NJ and your stepson has plans to work in PA after graduation so I’m not sure I understand your worry. Are you sure you’re not projecting your fears for your daughter onto your stepson?
@austinmshauri my husbands kid and his worry more than mine-- like I said he is the one that is so upset; if he wasn’t I wouldn’t be either – don’t worry my kid makes me crazy too and the LD (and having been in the middle of the divorce from her father) is the reason she got any leeway at all. And her gig is now up, she moved out, I am done paying.
She was also paying much of her own way (cc was 1-2 classes at a time and it was all I paid for). What her father allowed her to do at his home was not in my control. My understanding is she was paying her own living expenses. You cannot really compare a NT kid with one who struggles with LDs and mental health issues. If you are saying we gave her more leeway I assure you we have not.
You’re overprotective and helmets don’t matter in many ski accidents. Helmets don’t protect you from a tree well or an avalanche or falling in a crevasse. They don’t protect your legs if your bindings don’t release. The literature generally finds little to no benefit in preventing spinal injury. Even in terms of head trauma, they’re of limited utility. They’re only rated up to 15mph in a head on collision and recreational skiers routinely go far faster.
All you can do is warn him that skiing out of bounds or without a ski pass will result in a citation at the very least, an arrest if authorities want to take it to the next level (and the skiing out of bounds is a BIG deal these days because of the cost of rescues). Yell at him, warn him, then back away.
Backcountry skiing isn’t illegal. Helmets are almost the norm now too. IME it is the oldies in their 80’s ski outfits that won’t wear helmets, youngster have been brought up with it as the norm.
Most backcountry skiing can be illegal without a permit. You are either on national forest or private land. Certainly skiing out of bounds near a resort is illegal as the resorts have leases on all that land.
OP’s son doesn’t seem to want to go to the back country for the experience, but to avoid paying for lift tickets.
Anyone that is prepared to walk up a hill and ski down it is no slouch. Good for him. Backcountry skiing is very common here. I doubt money is the driving factor.
“OP’s son doesn’t seem to want to go to the back country for the experience, but to avoid paying for lift tickets.”
I think there is too little info here to know what exactly OP’s stepson does skiing-wise. OP mentions him being helmet-less in the context of a photo.
I say instead of worrying so much, just let him know your support stops on July 1st. As long he doesn’t ask you for financial support or move back home then there isn’t anything you need to. When he runs out of money or what is making is not able to support the lifestyle he has grown accustom to then he will figure out what he needs to do. That is if you do not do anything to enable the lifestyle you do not support.
And Alta got 14" since 4 am! Really hoping he is in Utah LOL.
This is a slight digression, but fortunately most skiiers do wear helmets now. While nothing is perfect, they can not only keep you warm, but provide some protection against concussions, lacerations, fractures, etc. As I mentioned upthread, we are skiiers. And our family happened to be on the slopes in late 1997-early1998 over winter break when both Sonny Bono and Michael Kennedy died from head injuries on the slopes. Think what you will about his choice to love the slopes, but do what you can to encourage him to wear a helmet. All.the.time. Lets hope he took it off for a still photo.